​I don’t know what it is about my luck during this trip, but my flight/entire travel experience on the way home was an absolute shit show. The initial Liat Airlines flight from St. Vincent to Barbados was delayed (with no communication from ground crew) for an hour and a half. We finally took off and landed at Barbados’ BGI airport a half hour later, where I proceeded to wait a whopping 45 minutes for my checked bag to make it to the carousel so I could transfer it from Liat to JetBlue. By the time I made it to JetBlue’s check-in counter the place was “closed” and the only agent around told me I was too late to check my bag. With no cell phone to use as a mobile boarding pass (and the check-in kiosks shut down) I had to beg this woman to print me a boarding pass as I converted my checked bag to a carry on by handing a vacationing family my 12oz bottle of suntan lotion, and gifting one of my very nice Gerber spring assisted knives (my everyday carry) to a guy who was waiting to pick up his brother curbside at the airport. Having ridded myself of the only two non-carry-on-able items I had, I rushed through security and Customs, making a break for the New York bound flight’s gate. To arrive and find out the flight was nearly an hour delayed pissed me off to no avail as I sweated profusely. It seems nobody in the Caribbean has ever heard of air conditioning, and the 85-degree temperatures in the airport combined with the stress of my time there had caused me to sweat through my light t-shirt. The flight to JFK was relatively simple, though I waited over an hour to collect my checked bag in Customs and then re-check it for the flight to Boston. The jumper to Boston followed suit with delays, taking off almost two hours late, but I will say that if I didn’t fly on 100+ other flights a year I’d be even more irate towards these airlines for the way my trip has been. I still plan to write JetBlue an email regarding their performance over the past two weeks. Thankfully a friend picked me up at Logan and gave me a ride home where I dropped off my suitcase, grabbed a change of clothes, and drove up to sleep on my parents couch so that I could see my mom first thing the next morning.

All in all, I think that the cost of this sailing program was in fact worth it. I haven’t run the exact numbers yet, nor filed a complaint with JetBlue for them to reimburse the cost of my missed flight on the way down, but I think it’s fair to say that it cost about $2,700 cash (flights, lodging, meals, incidentals, taxi rides, drinks) and 68,000 JetBlue miles. I haven’t been on a sailboat in half a decade, and haven’t been taught about the principles of sailing in fifteen years. Being forced to read through the American Sailing Association textbooks, study the material, and perform the physical maneuvers on a boat that’s roughly the size of what I’d like to buy was well worth the cost to play. I mentally confirmed the fact that it’s something I’m interested in pursuing, and found myself day dreaming as we sailed about being out on my own with no land in sight, making my way to the other side of the ocean. I think that it will certainly have mundane moments during long days in calm waters, and without a doubt will include instances of incredible fear and trials. Am I crazy? Yes, probably, but this isn’t one of those ideas I’m ready or willing to let go of.

To restate for good measure: There’s no gun to my head, and no timeline I’m forced to meet. This is not a trip I’ll undertake without complete and proper preparation, readiness, and safety measures in effect. At the end of the day the idea of the adventure, the idea of the stories, challenges and experiences call to me in a way I haven’t experienced since first reading Bill Bryson’s A Walk In The Woods a year before my Appalachian Trail hike. With first hand sailing experience rejuvenated and the continued interest confirmed in my own mind, I’ll now turn my sights towards researching and purchasing a boat… a huge undertaking on its own that I won’t pull the trigger on until ideally next summer. I think it’s immensely important that I spend my time sailing my own boat, finding its weaknesses, making upgrades, and learning how she sails. I can spend my summers, where I usually take July & August off, sailing off the coast of New England in rougher/colder seas, and can push myself to learn on a yacht that isn’t a commercially operated sailboat kept to 100% for the customer’s sake. The Barefoot school served its purpose completely by getting me on a boat, expanding my base knowledge of sailing to one of sailing, rigging, navigation, chart reading, basic boat diesel engine repair, etc. It gave me the hands on experience I didn’t yet have on this scale, and got me even more excited to pursue this dream.

On a final note, thank you for following along for another quick adventure, I hope it was at least somewhat entertaining for you and didn’t overwhelm your inbox for those that are still subscribed to updates. The next trip will be coming up in December with Santa and I’ll be blogging a little bit between now and then as he and I prepare to do a hike in a manner that few people seem to have done before... Hopefully there’s some more good reading & photos to come.

​With it being the last morning aboard the boat, there was no rush to wake up or get underway. The route back to Blue Lagoon on St. Vincent was all of 6 nautical miles, and was something we could accomplish in just over an hour if the wind cooperated. As Chris took one final swim in the greenish-blue water of Admiral Bay I used a scrub brush and a bucket of seawater to wash off the cockpit deck on the boat. Each of us stripped our beds of sheets and stuffed them into pillow cases for the Barefoot Sailing employees to have an easier time cleaning the boat and getting it ready for its next trip out. We reconvened on deck for a final breakfast together, doing our best to consume the miscellaneous foods that we still had stored in the refrigerator... while everything on the boat is miniature sized, it wasn’t until the last day that we dug down deep enough in the fridge to find a half dozen little containers of fruit yogurt, a welcome surprise after a week of a low-dairy diet. We talked as we sat in the morning sunshine eating, and watched as a small red dinghy floated around in the harbor with a man aboard approaching each yacht. He rowed up to us and offered fresh croissants and baguettes for purchase, and while I wasn’t particularly interested, José jumped at the opportunity and bought us a round of croissants for $20 EC. Though they were by no means delicious, and instead had some faint taste of raw dough or even plastic, the experience was interesting and I can now say I’ve purchased dessert bread from “D Bubble The Bread Man” in Bequia (bek-way).

As Rory, Chris, and José returned below deck to finish their packing, Jimmy motioned to me to start the diesel as he wandered to the foredeck and began raising the anchor. After it was up and secured he simply said “Take her out” and went below deck. I feel like he and I had developed a strange and almost cryptic form of communication this week, and though I didn’t always understand him the first time he said something, I had a quiet appreciation for our lack of long conversations. I followed the Captain’s orders and brought Mango out through the harbor moorings and past the old working ships, steering her into the wind and raising the mainsail for us to begin our trip back to the Blue Lagoon harbor that Barefoot and our boat call home. I aimed us out and around the cardinal markers that delegate the harbor channel, and kept a keen eye out for scuba divers in the area as we kept the diesel on in tandem with the sail for power. As we rounded the horn of the harbor the mountainous cliffs of Bequia towered over us on the starboard side, looking beautiful and simultaneously killing all hope we had of direct wind to the sail. By the time we were around the horn our entire group was above deck, Rory and Chris relaxed on the benches while José used his compact GoPro camera to film our surroundings. Jimmy sat quietly at the stern of the boat and listening to conversations, occasionally pointing his finger to a new heading for me to aim our bow towards.

We fought with the wind for the majority of our 100-minute ride across the channel, ultimately leaving the engine running at low RPMs to create some sense of wind for the sail to catch. During my time at the helm I watched our weathervane stumble like a drunken sailor, spinning haphazardly in circles, as unsure as any of us as to the direction the wind was actually coming in. The “gusts” of wind measured in at a whopping 5 knots, and I was seeing steady readings of 2kts for the majority of our trip. Eventually I wanted to hand off responsibility of the wheel so I could take some final pictures, and Rory took over for almost all of the remaining time aboard. We pulled back into Blue Lagoon’s channel shortly after 1130 and were almost immediately greeted by a dinghy of Barefoot staff members who made quick work of taking over the helm and engine controls, tying off fenders on the port side of the boat, and swinging us in a circle before backing the 43-foot yacht into the dock alongside a catamaran and second monohull that were both being prepared for charters. Chris later related the handover of control to that of pirates taking our ship hostage. Once we were tied off to the dock we began unloading our personal gear, lifejackets, snorkeling equipment, and remaining food before gathering on the stern’s transom (rear most deck by sea-level) for our last group photograph.

After settling up on our payments to Barefoot and receiving our signed American Sailing Association log book, certifying that we had completed the 101, 103, and 104 Bareboat chartering requirements, we gathered at the Driftwood bar for a few beers before going off in different directions. We were joined at the bar by a great guy named Seth, the manager of Barefoot, and had the pleasure of listening to many of his stories of working in Her Majesty’s Royal British Navy fighting aboard the famous Conqueror submarine. Seth, then in his early 20s, sailed around the Mediterranean with the hopes of a circumnavigation the world but ended up in the Caribbean and has never looked back. After an hour or two of cold beers with Rory, Chris, Jimmy, and Seth, José and I decided it was time for lunch and walked down to Blue Lagoon to have a quick bite to eat before he left for the airport. Finishing delicious cheeseburgers, we walked back to Barefoot where Chris had arranged a cab to take us to their hotel and airport respectively.

I had attempted to find an earlier flight home but all seemed to be sold out, so I joined Chris and Rory at the Beachwood Hotel about a mile away from the airport on St. Vincent. For the price of $104 a night I got a sizable hotel room at a quiet resort right on the Caribbean waters. A small pool and deck were accessible through their covered bar/restaurant area where Chris, Rory, and I sat for a late dinner as a local musician serenaded the small group of patrons. We talked for an hour or two about our home lives, spending very little time discussing the boat that we had spent the past week on. It was nice to color outside the lines of conversation topics and before I knew it the clock showed half past 10. I said my final goodbyes to the couple, hugging each of them before returning to my room and packing up for an early flight tomorrow morning.

With absolutely no way of setting an alarm, I’m sincerely hoping I manage to wake up on time tomorrow , as I wouldn’t want to miss my flight. I've had such a great time this week but there's no doubt in my mind, I’m ready to go home.

Fully packed, trying to convey the tight constraints of the berth I had all week.

I didn’t post a blog last night due to time constraints, and an abundant lack of cell service (my phone showed EDGE, or 2G, which was the data speed I used to blog on my BlackBerry with in 2007). The average post takes me over an hour to compose, edit photos for, and publish; a time commitment that makes a 10pm bedtime closer to midnight in the blink of an eye. The bay at Mayreau Island was unbelievably quiet, with the calmest waters we’ve had yet on this trip. I slept like a baby in my small bunk until my alarm went off at 0500hrs. Why on God’s green earth would I wake up at 5 if I didn’t absolutely have to, you ask? Because how often do I get the opportunity to photograph the sunrise against a foreground of turquoise blue water and swaying palm trees!

I hopped in the dinghy off Mango’s stern at 0515, and in an effort to not wake any of the residents of the 20+ other yachts, decided against starting the engine and instead used the oars to get myself to shore. I tied the dinghy up to the base of a palm tree and spent the next hour photographing the same scene as the water movement, cloud cover, and sunlight changed into an immaculately picturesque morning. As I returned to the dinghy, loading my camera set up and tripod into the bow, I realized that in my efforts to quietly escape the yacht, I had forgotten to grab the actual key to the outboard motor. This meant I’d be rowing back out to the boat, against the current. I suddenly pictured myself as Tom Hanks in the film Cast Away, floating on my raft in the same way he floated on the lashed fallen trees, rowing his way towards the massive wave that had kept him captive on the island until that blue piece of Porta-Potty washed ashore and became his sail. Yes, in real life I was nowhere near Tom’s level of desperate or stranded, but it certainly helped me mentally face the fate of rowing against the tide out to the boat. I pushed off the white-sanded bottom of the ocean and launched the dinghy forward, alternating sides a few times before the oar became lodged in the sand and I continued to float out past it. Hind sight being 20/20, there were a hundred different ways I could have handled this and I of course chose the wrong one, jumping off the side of the dinghy into what I thought was shallow water in order to get the oar without losing the boat. It wasn’t until my upper torso was soaked in salt water that I realized my iPhone was in my left pants pocket, and subsequently submerged like the Beatles’ Yellow Submarine. Long story short, phone got fried in the salt water, which is why I’ve disappeared from the face of the socially connected planet for the last 5 days. Rest in peace, phone, we had a great 20 months together. I’ll remember you fondly.

With over 20 miles of sailing to do today, Jimmy wanted anchors up and sails raised by 0745 this morning. Despite my defeated and sad mental state after the events with my phone, I jumped to the bow and raised the anchor as José navigated us out of the harbor. With little wind and a long ways to go, we motor-sailed with the engine running at low RPMs and mainsail raised for about an hour. Passing back by Tobago Cays we continued on towards Petite Canouan, at which point I took over at the helm and held our 45-degree compass heading. The seas were calm, probably the smoothest we’ve had all week, and the wind held steady at 10 knots with “gusts” of 13kts… the sailing was by no means thrilling. I actually was feeling comfortable enough with the boat and our vastly open surroundings to power up the AutoPilot and let the GPS driven drive gear maintain our course back towards Bequia where we had come through on our first night at sea. The ride back took 5 and a half hours, during which I held position at the helm, napped, read through our ASA104 course textbook, and otherwise just relaxed as the world went by. We were forced to trim the sails for a close-haul point of sail, as close as humanly possible to the wind itself… the result being slow speeds and anticlimactic movement.

Shortly after 1330hrs we dropped anchor in the harbor, and after a quick ham and cheese sandwich, I applied more sunscreen and lay out on the deck just forward of the mast for an hour long nap in the Caribbean sun. Waking up to find everyone else napping, I did some final review for the last written exam of the week before Jimmy administered it to us mid-afternoon. The test is designed to be the culmination of everything learned throughout the week/other two textbooks, and consisted of 50 true/false questions and 50 multiple choice. Despite knowing the material of the book rather well, and having thoroughly reviewed the practice exams, I was surprised to find that the test itself had little at all to do with the book or study guides. The grand finale of the ASA exams for the week consisted of 5 questions regarding a weather map/chart, distances between locations, gallons of fuel burned to motor between them, time spent sailing, and exact coordinate locations. I can honestly say I have not had to do that kind of math in a very long time, and the death of my iPhone left me doing hand-written long division for the first time in almost a decade. (Side note, when checked with Rory’s iPhone, my math was actually pretty much spot on). I again didn’t do as well as I had hoped, but given the subject matter’s misalignment from what I read and studied, per the courses requirements, I’m ok with the fact that I passed at all. I’ve never been one for written tests, and have instead always succeeded with hands-on testing, a fact that remains true to my sailing skills this week, which I think Jimmy is well aware of.

After finishing and reviewing the test with Rory, Chris, José, and Jimmy, I showered quickly and got dressed for the evening. We ate an amazing dinner on board prepared by Chris and José, a pasta dish with ground beef and tomato sauce, and homemade guacamole that José whipped up in a bowl with these incredibly sweet avocados he had purchased a day or two ago. Life was good, and we drank and ate together in the boat’s cockpit as the sun set over Admiral’s Bay. After dishes were washed we piled into the dinghy and made our way to Coco’s, a little restaurant/bar establishment that’s right on the water to the north side of the harbor. An advertisement had promised live music, so we grabbed a table on the porch and listened to the great sounds of a man and his keyboard as he covered decades of classics. Listening as he covered Sinatra, Clapton, Bob Marley, and even Cat Stevens. As the sea breeze picked up off the harbor, hand made lanterns swayed above patio tables and cast their unique shadows on the walls of the building as the music played in the background. We ordered drinks, my Jack & ginger being pleasantly stiff, and before long a small birthday “cake” had arrived for Christina. Cold vanilla bean ice cream melted to a drizzly mess over a warmed chocolate brownie, and our five spoons dug into it as if we hadn’t eaten in a week. Another round of drinks was ordered, and I sat back in my chair thinking to myself how lucky I was to be there. A light rain began falling outside as I considered the simple fact that a week ago I didn’t know any of these people, and now we learn, eat, share, and tease like a family. It’s such a unique situation to be in, and an amazing opportunity to be faced with the task of learning and flourishing amongst complete strangers… It took a few days to find a groove, but I’m so happy we did.

Taking the dinghy ride back to the boat in a light rain, I retired to my berth to write this post on my laptop, having given the iPhone a ounce of hope as I tried yet again to turn it on. Oh well, looks like I made an $850 mistake, and it’s certainly one I’ll never make again; thankfully the Canon dSLR lives on strong, though that camera and I have been through hell and back together already so I wasn’t too concerned for it this week. Tomorrow morning we’ll rise late, set sail mid-morning, and be back at the docks at Barefoot Offshore Sailing School by noon to disembark the boat.

Going to sleep smiling, happy that I challenged myself to come down here alone and see if I want to have what it takes to complete my next big adventure.

I spent the night with the air conditioning cranked to combat the humidity and heat of the island. Waking up around 7, I was confused for a moment as to where I was; the loud sound of rain on a tin roof gave me the nostalgic feeling of being in an A.T. shelter, which really threw me for a loop as I was still half asleep. A quick and cold shower was an interesting way to start my day before packing up my gear and heading downstairs to check in with the registration office and pay the remaining 50% of my course bill. Total for the 7 day sailing program and certifications will be around $1,800, which I don't particularly think is bad for a week long Caribbean vacation that includes an immense amount of hands on boat training. I visited the Barefoot compound's restaurant Driftwood and paid a heft fee for two chocolate chip pancakes and orange juice, sitting under a large porch awning as the rain battered the leaky roof. At some point José came down and joined me, though we sat in relative silence watching gusts of wind and precipitation blow through Blue Lagoon.

Around 1000hrs Rory and Christina (Chris) joined us on the porch as we awaited the arrival of Jimmy, our instructor for the week. A salt and peppered hair gentlemen with darkly tanned skin, standing about 5' 6", Jimmy's of South American origin and speaks with a heavy Caribbean accent. Large black ink tattoos sprawl his forearm, and his level of eye contact while speaking is piercing, reminiscent of a teacher I had in high school. The 5 of us sat at a table under the awning at Driftwood and began discussing the week ahead, his expectations, what our expectations should be, and the general overview of our boat, Mango 2, before we went to the docks to stow our gear. It was about this time that my phone rang, which I ignored due to the important nature of the conversation I was involved in. I looked down a few minutes later to see that I had 7 missed calls from my dad, which I knew was not a coincidence or accidental thing. I sent a quick text asking if he was OK, and excused myself, apologizing profusely, when he responded with 'No.'

My parents were in Way-Upstate New York for a tandem bicycle rally this weekend, getting one last morning ride in before heading back to Boston. Riding in a group on a country farm road, my dad at some point steered a little too far to the right of the shoulder, and the front wheel dropped some 2" off the blacktop into a rocky bed of gravel. With their 20+ mph momentum the rocks sucked in the front tires and dragged the bike down a 6-foot embankment where they crashed, laying the bike down on the left side. While the details I have of the incident aren't phenomenal due to limited cell reception and only a few status update text messages, the take home facts were that my mother lost consciousness for a few minutes and the ambulance drivers that arrived on site made the decision to call in a MedFlight to bring her to a Rochester, NY trauma center by helicopter. She was given a full work up of scans, pain meds, etc, and will spend the next days in the hospital before returning to Boston. Speaking to my dad late last night he told me she was doing better, her arm broken and in a sling, with a collar on to keep her neck braced. Being 3,000 miles away on a boat with limited communications is not the ideal place to be, but my dad stressed that the most important thing for me was to focus and do what I came here to do.... So that, and maintain as frequent communication as possible, is what I'll do. Love you, mom.

After stowing our luggage on Mango we went over final briefings, grabbed snorkeling gear, and cast off our bow lines. Jimmy is in the forward berth, a large bed in the bow, Chris and Rory and José are in bedrooms under the aft cockpit (where the steering wheel is), and I've got a small little bedroom the size of my walk-in closet at home with two little bunk beds. I've got two windows that open onto the bow deck, and a 12volt fan that creates a good breeze in an otherwise stagnant room. We used the diesel engine to power out into the harbor before 'heading up', or steering into the wind, in order to raise the mainsail. Mango is in the 45' range, with all of her sail lines routed back to the cockpit for easy operation. The boat is actually laid out quite nicely for even a single person to operate. Our first raising of the sail wasn't exactly smooth, but we have a week to get better at it. After getting some wind power we killed the engine and sailed out between the channel markers to the bay, raising the jib, a smaller and lighter sail forward of the mast, and setting course for a small island a few hours north of St. Vincent.

We took turns at the helm, each steering for 30 minutes or so, and encountered lots of different weather. José took us out of the harbor under light wind and calm waters, which Rory continued further out. It was comedic to hear Chris call out to her husband when he veered off course or a wave pushed him away from the direction of our destination even for a second, as she sat further up in the cockpit and observed. By the time it was my turn, the fair seas had turned to whitecaps and 6-8' waves that rocked the boat drastically. Wind speeds were holding steady at 16 knots with gusts as high as 22kts as I did my best to fight the current underneath and keep the rudder straight. It'll take some practice to learn how to give and take with the steering wheel as we encounter different kinds of seas. We made it to the harbor of the small island Bequia, and spent an hour or two practicing tacking, the act of turning the boat's course by bringing the bow through the wind. It was certainly a different experience to tack on a boat that was 2-3x the length of the boats I sailed during my summers as a kid, and infinitely smoother to do. We eventually dropped our sails and motored into the harbor, dropping our anchor in 8-feet of turquoise blue water, and quickly changing to bathing suits to go snorkeling around the boat. Words cannot describe how enjoyable it is to jump off the back of the boat into relative bathwater... it's infinitely better than the frigid summer water temperatures off the coast of Massachusetts.

After drying off, Jimmy administered our ASA101 course written exam, a multiple choice test of 100 questions, which took me about 25 minutes to complete. I got a 95%, above the 80% required to pass, though two of my incorrect responses were due to messing up which question number and letter bubble I was filling in. C'est la vie. We took the dinghy into the dock and went to a small restaurant called Maria's where we had snapper fish and cold beer for dinner. I was relatively absent (thankfully) from the dinner conversations about American president race politics, and called my dad to check in on mom. Zipping back across the harbor around 2100hrs, I stared up in awe of the constellations in the sky above. I've never slept on a sailboat overnight before, so I'm wondering how I'll take to the incessant rocking.

Day 1 went well, all things considered, and I'm excited to see where tomorrow takes us.